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Sulfonimidates

Sulfonimidates. An accessible Synthesis of N-tosyl O-alkyl Sulfonimidates From Sulfinate Esters, Using Chloramine-T. By Daniel Savino. Background. Sulfonimidates are alkylating agents. -R 2. Background. Sulfonimidates are difficult to synthesize

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Sulfonimidates

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  1. Sulfonimidates An accessible Synthesis of N-tosyl O-alkyl Sulfonimidates From Sulfinate Esters, Using Chloramine-T By Daniel Savino

  2. Background • Sulfonimidates are alkylating agents -R2

  3. Background • Sulfonimidates are difficult to synthesize Leca, D., Fensterbank, L., Lacote, E., Malacria, M.. Org. Lett.; (Communication); 2002; 4(23); 4093-4095

  4. Concept • Sulfinate esters can be attacked (nucleophilic?) by chloramine-T Εικόνα από τη βιβλιοθήκη Savino

  5. Simplicity Itself • Sulfinate ester + chloramine-T in CH2Cl2 (dropwise add’n) • Stir ~10 min. • Filter, rotovap, wash/rotovap and Kugelrohr. • Done! • Total time… ~2 hours

  6. Results • 76.6% yield • IR – Lack of sulfonamide peaks • NMR – Appropriate methyl peak for tosyl, diastereotopic triplet for the O-ethyl CH3

  7. Acknowledged • Dr. Tom Maricich • Dr. Galt

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